1,2-diphenyl-2-propen-1-one derivatives

Abstract

The present invention provides compounds represented by the following formula [I] or salts thereof which lower intraocular pressure by causing morphological change in trabecular meshwork cells. In the formula, R1 is H, lower alkyl, hydroxy, lower alkoxy or halogen, R2, R3 and R4 are H or lower alkyl, and . . . is a single bond or a double bond. When R3 and/or R4 is hydrogen, the amino can be protected by a protecting group.

What is claimed is:  
     
       1. A compound represented by the following formula or a salt thereof,                    
       wherein R 1  is hydrogen, lower alkyl, hydroxy, lower alkoxy or halogen, R 2 , R 3  and R 4  are the same or different and are hydrogen or lower alkyl, and  . . .  is a single bond or a double bond. 
     
     
       2. The compound or a salt thereof as claimed in  claim 1 , wherein R 3  and/or R 4  is hydrogen, and the amino group is protected by a protecting group. 
     
     
       3. The compound or a salt thereof as claimed in  claim 1 , wherein R 1  is a group selected from hydrogen, lower alkyl and halogen. 
     
     
       4. A compound or a salt thereof as claimed in  claim 1 , wherein the compound is 1-[4-[(E)-3-(dimethylamino)-1-propenyl]phenyl-2-phenyl-2-propen-1-one. 
     
     
       5. A pharmaceutical composition comprising a pharmaceutically effective amount of the compound or a salt thereof as claimed in  claim 1  as an active ingredient in combination with a pharmacologically acceptable carrier. 
     
     
       6. A method for improving aqueous humor outflow in a patient comprising administering to a patient a pharmaceutically effective amount of the compound or a salt thereof as claimed in  claim 1  as an active ingredient. 
     
     
       7. A method for lowering intraocular pressure in a patient comprising administering to a patient a pharmaceutically effective amount of the compound or a salt thereof as claimed in  claim 1  as an active ingredient. 
     
     
       8. A compound represented by the following formula or a salt thereof,                    
       wherein R 1  is hydrogen, lower alkyl, hydroxy, lower alkoxy or halogen, R 2 , R 3  and R 4  are the same or different and are hydrogen or lower alkyl,  . . .  is a single bond or a double bond, >X is >CHOH or >C═O, and when R 3  and/or R 4  is hydrogen, the amino group is unprotected or protected by a protecting group. 
     
     
       9. The compound or a salt thereof as claimed in  claim 1 , wherein R 2  is hydrogen. 
     
     
       10. The compound or a salt thereof as claimed in  claim 3 , wherein R 2  is hydrogen. 
     
     
       11. The compound or a salt thereof as claimed in  claim 1 , wherein both R 3  and R 4  are lower alkyl. 
     
     
       12. The compound or a salt thereof as claimed in  claim 3 , wherein both R 3  and R 4  are lower alkyl. 
     
     
       13. The compound or a salt thereof as claimed in  claim 10 , wherein both R 3  and R 4  are lower alkyl. 
     
     
       14. The compound or a salt thereof as claimed in  claim 1 , wherein the compound is 1-[4-[3-(dimethylamino)propyl]phenyl-2-phenyl-2-propen-1-one. 
     
     
       15. The method as claimed in  claim 6 , wherein the compound is selected from the group consisting of 1-[4-[(E)-3-(dimethylamino)-1-propenyl]phenyl-2-phenyl-2-propen-1-one and 1-[4-[3-(dimethylamino)propyl]phenyl-2-phenyl-2-propen-1-one. 
     
     
       16. The method as claimed in  claim 7 , wherein the compound is selected from the group consisting of 1-[4-[(E)-3-(dimethylamino)-1-propenyl]phenyl-2-phenyl-2-propen-1-one and-1-4-[13-(dimethylamino)propyl]phenyl-2-phenyl-2-propen-1-one. 
     
     
       17. The composition as claimed in  claim 5 , wherein the compound is selected from the group consisting of 1-[4-[(E)-3-(dimethylamino)-1-propenyl]phenyl-2-phenyl-2-propen-1-one and 1-[4-[3-(dimethylamino)propyl]phenyl-2-phenyl-2-propen-1-one.